Fmoc-POAC : [(9-Fluorenylmethyloxycarbonyl)-2, 2, 5, 5-tetramethylpyrro-lidine-N-oxyl-3-amino-4-carboxylic Acid] : A Novel Protected Spin Labeled β-Amino Acid for Peptide and Protein Chemistry
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概要
- 論文の詳細を見る
The stable free radical 2, 2, 6, 6-tetramethylpiperidine-N-oxyl-4-amino-4-carboxylic acid(TOAC)is the only spin labeled amino acid that has been used to data to successfully label peptide sequences for structural studies. However, severe difficulty in coupling the subsequent amino acid has been the most serious shortcoming of this paramagnetic marker. This problem stems from the low nucleophilicity of TOAC's amine group towards the acylation reaction during peptide chain elongation. The present report introduces the alternative β-amino acid 2, 2, 5, 5-tetramethylpyrrolidine-N-oxyl-3-amino-4-carboxylic acid(POAC), potentially useful in peptide and protein chemistry. Investigations aimed at addressing the stereochemistry of this cyclic molecule through X-ray diffraction measurements of crystalline and bulk samples revealed that it consists only of the trans conformer. The 9-fluorenylmethyloxycarbonyl group(Fmoc)was chosen for temporary protection of the POAC amine function, allowing insertion of the probe at any position in a peptide sequence. The vasoactive octapeptide angiotensin II (All, DRVYIHPF)was synthesized by replacing Pro^7 with POAC. The reaction of Fmoc-POAC with the peptidyl-resin occurred smoothly, and the coupling of the subsequent amino acid showed a much faster reaction when compared with TOAC. POAC^7-All was obtained in good yield, demonstrating that, in addition to TOAC, POAC is a convenient amino acid for the synthesis of spin labeled peptide analogues. The present findings open the possibility of a wide range of chemical and biological applications for this novel β-amino acid derivative, including structural investigations involving its differentiated bend-inducing characteristics.
- 公益社団法人日本薬学会の論文
- 2001-08-01
著者
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Paiva Antonio
Department Of Biophysics Universidade Federal De Sao Paulo
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TOMINAGA Mineko
Department of Biophysics, Universidade Federal de Sao Paulo
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NAKAIE Clovis
Department of Biophysics, Universidade Federal de Sao Paulo
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Schreier Shirley
Department Of Biochemistry Institute Of Chemistry University Of Sao Paulo
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Nakaie Clovis
Department Of Biophysics Universidade Federal De Sao Paulo
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Tominaga M
Department Of Biophysics Universidade Federal De Sao Paulo
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Tominaga Mineko
Department Of Biochemistry Institute Of Chemistry University Of Sao Paulo
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BARBOSA Simone
Department of Biophysics, Universidade Federal de Sao Paulo
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POLETTI Erick
Department of Biophysics, Universidade Federal de Sao Paulo
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ZUKERMAN-SCHPECTOR Julio
Department of Chemistry, Universidade Federal de Sao Carlos
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MARCHETTO Reinaldo
Department of Biochemistry, Institute of Chemistry
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Poletti Erick
Department Of Biophysics Universidade Federal De Sao Paulo
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Barbosa Simone
Department Of Biophysics Universidade Federal De Sao Paulo
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Marchetto Reinaldo
Department Of Biochemistry Institute Of Chemistry
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Zukerman-schpector Julio
Department Of Chemistry Universidade Federal De Sao Carlos
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